It is the intent of this proposal to develop the mono- and multiple carbanion chemistry of certain nitrogenous heterocycles including 1, 3-dialkylquinolines, papaverine, two Harmala alkaloids and their alkylated derivatives, and various alkylated and dialkylated pteridines; some of the latter will be substituted with amino and hydroxy groups. The study will involve the treatment of the above compounds with various basic reagents including, but not limited to, alkali amides in liquid ammonia, n-butyllithium in ethers, and lithiodialkylamides in ethers. The concept of selective metalations of the methyl groups of ethylated nitrogenous heterocycles will be refined as a function of steric hindrance of the heterocycle, the basic reagent, and the solvent. All of the carbonions formed in this study will be condensed with a variety of electrophiles including aldehydes, ketones, esters, alkyl halides, alpha, beta-unsaturated carbonyl compounds, and others to give new compounds, many of which may be suitable as medicinals. Many intermediates derived from these reactions should be capable of subsequent cyclization reactions to give novel, new heterocyclic compounds. Proposed convenient syntheses of folic acid and related pteridine containing compounds are described.